This comprehensive review surveys developments over the past decade in the field of naphthalene diimides (NDIs). It explores their application toward: supramolecular chemistry; sensors; host–guest complexes for molecular switching devices, such as catenanes and rotaxanes; ion-channels by ligand gating; gelators for sensing aromatic systems; catalysis through anion−π interactions; and NDI intercalations with DNA for medicinal applications. We have also explored new designs, synthesis, and progress in the field of core-substituted naphthalene diimides (cNDIs), and their implications in areas such as artificial photosynthesis and solar cell technology. Also presented are some interesting synthetic routes and procedures that can be used toward further development of NDI-bearing compounds for future applications. Finally, we conclude with our views on NDI chemistry for future research endeavors, and we outline what we believe are the key obstacles that need to be overcome for NDIs to see real world applications.

Functional Naphthalene Diimides: Synthesis, Properties, and Applications

We have developed a new methodology that enables the synthesis of any sequence of metal porphyrin arrays starting from a common key molecule. Using this method, we prepared porphyrin dimers and trimers with varying component unit sequences via consecutive Suzuki coupling reactions using the same key porphyrin compound under the same reaction conditions. The key porphyrin compound was synthesized on a gram scale in one batch, and the coupling reactions afforded the desired oligomers in good yields. Thus, the prepared porphyrin arrays showed unique physical properties depending on the sequence of the central metals. The reaction is potentially applicable for the automated synthesis of porphyrin arrays.

Synthesis of a series of Zinc(II)/freebase porphyrin dimers and trimers with programmable sequences from a common key molecule.

Graphene oxide (GO) is a carbon-based material with good electronic, chemical, and fluorescence properties and high potential as biosensor applications. Graphene oxide was modified by strontium oxide (SrO-GO) and iron oxide (Fe3O4−GO) for screen-printed carbon electrode (SPCE) modification. The characterization of graphene oxide and nanocomposites were conducted by X-Ray diffraction, UV-Vis, scanning electron microscopy, and energy dispersive X-Ray spectroscopy. The GO nanocomposites-based-modified SPCE was applied in the electrochemical measurement of Cefixime (Cephalosporin antibiotic groups) by cyclic voltammetry. The result of cyclic voltammetry measurement showed good sensitivity and high stability for SPCE in order from the highest is SrO-GO > GO > Fe3O4-GO. The SrO-GO nanocomposites-modified SPCE indicated the highest sensitivity and high stability due to the synergy effect of strontium and GO properties, which enhances electrocatalytic properties in the oxidation and reduction of cefixime. Moreover, strontium nanoparticles enhance the Fermi level of the GO, therefore occupying it with more electrons and increase the electron transfer.

Graphene oxide based nanocomposite modified screen printed carbon electrode for qualitative cefixime detection

Targeting the development of stimulus-responsive molecular materials with electronic functionality, we have synthesized and studied the redox and electronic properties of a new bimetallic iron hydrophobe [FeIII2(LN4O6)] (1) The new H6LN4O6 ligand displays bicompartmental topology capable of accomodating two five-coordinate HSFeIII ions bridged by tetraaminobenzene at a close distance of ca 8 A We show that the metal-based reduction processes in (1) proceed sequentially, as observed for electronically coupled metal centers This species forms a well-defined Pockels-Langmuir film at the air–water interface, with collapse pressure of 32 mN m−1 Langmuir–Blodgett monolayers were deposited on gold substrates and used to investigate current–voltage (I–V) measurements This unprecedented bimetallic hydrophobe [FeIII2(LN4O6)] (1) shows unquestionable molecular rectification and displays a rectification ratio RR between 2 and 15

Observation of current rectification by the new bimetallic iron(III) hydrophobe [FeIII2(LN4O6)] on Au|LB-molecule|Au devices

Heterotrimeric G-proteins are ubiquitously expressed in several cancers, and they transduce signals from activated G-protein coupled receptors These proteins have numerous biological functions, and they are becoming interesting target molecules in cancer therapy Previously, we have shown that heterotrimeric G-protein subunit alphai2 (Gαi2) has an essential role in the migration and invasion of prostate cancer cells Using a structure-based approach, we have synthesized optimized small molecule inhibitors that are able to prevent specifically the activation of the Gαi2 subunit, keeping the protein in its inactive GDP-bound state We observed that two of the compounds (13 and 14) at 10 μΜ significantly inhibited the migratory behavior of the PC3 and DU145 prostate cancer cell lines Additionally, compound 14 at 10 μΜ blocked the activation of Gαi2 in oxytocin-stimulated prostate cancer PC3 cells, and inhibited the migratory capability of DU145 cells overexpressing the constitutively active form of Gαi2, under basal and EGF-stimulated conditions We also observed that the knockdown or inhibition of Gαi2 negatively regulated migration of renal and ovarian cancer cell lines Our results suggest that small molecule inhibitors of Gαi2 have potential as leads for discovering novel anti-metastatic agents for attenuating the capability of cancer cells to spread and invade to distant sites

Small Molecule Inhibitors Targeting Gαi2 Protein Attenuate Migration of Cancer Cells

Four different porphyrin-imide dyads bearing different central metals (zinc or rhodium) and different substituents on the porphyrin macrocycles (tert-butyl or methoxy) were synthesized for single molecular diode measurements. The molecules were designed to separate the donor component (porphyrin) from the acceptor component (imide) by bonding in a perpendicular arrangement, thus enhancing the rectification properties. UV/Vis absorption spectra and density functional theory calculations showed that the design was successful and that the molecular orbitals of the dyads were the summation of the two components, with minimal interaction between them. The effect of the central metal was found to be significant, with the lowest energy absorption for the zinc dyads being attributed to the mixed state of charge transfer from porphyrin to imide and the Q band, whereas that of the rhodium dyads indicated insignificant charge-transfer character.

Design and Synthesis of Perpendicularly Connected Metal Porphyrin–Imide Dyads for Two‐Terminal Wired Single Molecular Diodes

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Design and Synthesis of Perpendicularly Connected Metal Porphyrin–Imide Dyads for Two‐Terminal Wired Single Molecular Diodes